WO1998016202B1 - Fusogenic liposome composition and method - Google Patents
Fusogenic liposome composition and methodInfo
- Publication number
- WO1998016202B1 WO1998016202B1 PCT/US1997/018838 US9718838W WO9816202B1 WO 1998016202 B1 WO1998016202 B1 WO 1998016202B1 US 9718838 W US9718838 W US 9718838W WO 9816202 B1 WO9816202 B1 WO 9816202B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- hydrophilic polymer
- liposomes
- chains
- liposome
- Prior art date
Links
- 239000002502 liposome Substances 0.000 title claims abstract 33
- 239000000203 mixture Substances 0.000 title claims abstract 24
- 230000000799 fusogenic Effects 0.000 title claims abstract 3
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract 27
- 210000004027 cells Anatomy 0.000 claims abstract 22
- 229920001600 hydrophobic polymer Polymers 0.000 claims abstract 17
- 239000011248 coating agent Substances 0.000 claims abstract 8
- 238000000576 coating method Methods 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 230000004927 fusion Effects 0.000 claims abstract 4
- 210000000170 Cell Membrane Anatomy 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 230000027455 binding Effects 0.000 claims 17
- 239000003446 ligand Substances 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 11
- -1 polymethyloxazoline Polymers 0.000 claims 9
- 150000002632 lipids Chemical class 0.000 claims 8
- 239000000725 suspension Substances 0.000 claims 6
- 239000012528 membrane Substances 0.000 claims 4
- 239000003638 reducing agent Substances 0.000 claims 4
- 239000002202 Polyethylene glycol Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229920001223 polyethylene glycol Polymers 0.000 claims 3
- LAQPKDLYOBZWBT-NYLDSJSYSA-N (2S,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydrox Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]([C@@H](NC(C)=O)C=O)[C@@H]([C@H](O)CO)O[C@H]1[C@H](O)[C@@H](O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O1 LAQPKDLYOBZWBT-NYLDSJSYSA-N 0.000 claims 2
- 210000003743 Erythrocytes Anatomy 0.000 claims 2
- 229940014144 Folate Drugs 0.000 claims 2
- 102000006815 Folate receptors Human genes 0.000 claims 2
- 108020005243 Folate receptors Proteins 0.000 claims 2
- 206010018910 Haemolysis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 210000004698 Lymphocytes Anatomy 0.000 claims 2
- 229920000272 Oligonucleotide Polymers 0.000 claims 2
- 229920001451 Polypropylene glycol Polymers 0.000 claims 2
- 230000009089 cytolysis Effects 0.000 claims 2
- 229920000359 diblock copolymer Polymers 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000002019 disulfides Chemical class 0.000 claims 2
- 230000002708 enhancing Effects 0.000 claims 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 2
- 235000019152 folic acid Nutrition 0.000 claims 2
- 239000011724 folic acid Substances 0.000 claims 2
- 230000002949 hemolytic Effects 0.000 claims 2
- 230000002209 hydrophobic Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000002934 lysing Effects 0.000 claims 2
- 102000006240 membrane receptors Human genes 0.000 claims 2
- 108020004084 membrane receptors Proteins 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 210000004881 tumor cells Anatomy 0.000 claims 2
- 229940072107 Ascorbate Drugs 0.000 claims 1
- 229960002433 Cysteine Drugs 0.000 claims 1
- 206010015866 Extravasation Diseases 0.000 claims 1
- RWSXRVCMGQZWBV-WDSKDSINSA-N Glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims 1
- 229960003180 Glutathione Drugs 0.000 claims 1
- 108010024636 Glutathione Proteins 0.000 claims 1
- 229940031574 HYDROXYMETHYL CELLULOSE Drugs 0.000 claims 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000004698 Polyethylene (PE) Substances 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- 210000003324 RBC Anatomy 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229920002083 cellular DNA Polymers 0.000 claims 1
- 229920002092 cellular RNA Polymers 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000036251 extravasation Effects 0.000 claims 1
- 235000003969 glutathione Nutrition 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 claims 1
- 229920000068 poly(2-ethyl-2-oxazoline) Polymers 0.000 claims 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920000023 polynucleotide Polymers 0.000 claims 1
- 239000002157 polynucleotide Substances 0.000 claims 1
- 229920001955 polyphenylene ether Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 229920003288 polysulfone Polymers 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- 230000001737 promoting Effects 0.000 claims 1
- 235000018102 proteins Nutrition 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 229920000428 triblock copolymer Polymers 0.000 claims 1
- 210000000805 Cytoplasm Anatomy 0.000 abstract 1
Abstract
A fusogenic liposome composition for delivering a liposome-entrapped compound into the cytoplasm of a target cell is described. The liposomes have an outer surface coating of chemically releasable hydrophilic polymer chains which shield hydrophobic polymers on the liposomes outer surface. Release of the hydrophilic polymer chains exposes the hydrophobic polymers for interaction with outer cell membranes of the target cells to promote fusion of the liposome with the target cells. Also disclosed is a method for using the composition to deliver a compound to target cells, and a method for selecting suitable hydrophobic polymers for use in the composition.
Claims
1. A liposome composition for fusion with a target membrane, comprising a suspension of liposomes designed for targeting to the target membrane, where each liposome (i) contains a therapeutic agent entrapped in the liposomes, and (ii) is composed of vesicle-forming lipids, a portion of the lipids derivatized by a diblock copolymer composed of a hydrophobic polymer chain covalently bound to the lipid and a hydrophilic polymer chain, the hydrophobic and hydrophilic chains being joined by a chemically releasable bond for release of the hydrophilic polymer chains and exposure of the hydrophobic polymer chains.
2. The composition of claim 1, wherein the liposomes are further composed of vesicle-forming lipids having a hydrophilic polymer chain linked to a vesicle-forming lipid via a chemically releasable bond.
3. The composition of claim 1, wherein said releasable bond is a disulfide bond or a pH sensitive chemical linkage.
4. The composition of claim 1, wherein said hydrophilic polymer chains are composed of a hydrophilic polymer selected from the group consisting of polyvinylpyrrolidone, polyvinylmethylether, polymethyloxazoline, polyethyloxazoline, polyhydroxypropyloxazoline, polyhydroxypropylmethacrylamide, polymethacrylamide, polydimethylacrylamide, polyhydr- oxypropylmethacrylate, polyhydroxyethylacrylate, hydroxymethylcellulose, hy- droxyethylcellulose, polyethyleneglycol, and polyaspaitamide.
5. The composition of claim 4, wherein said hydrophilic polymer chains are composed of polyethylene glycol chains having a molecular weight of between 500-10,000 daltons.
6. The composition of claim 1, wherein said hydrophobic polymer is selected from the group consisting of polypropylene oxide, polyethylene, polypropylene, polycarbonate, polystyrene, polysulfone, polyphenylene oxide and polytetramethylene ether.
7. The composition of claim 6, wherein said hydrophobic polymer is polypropylene oxide having a molecular weight of between 500-3,000 daltons. 46
8. The composition of claim 1, wherein said hydrophobic polymer is a linear polymer effective to cause hemolysis of red blood cells when a water-soluble triblock copolymer containing the hydrophobic polymer and hydrophilic polymer chains joined to opposite ends of the hydrophobic polymer chains by disulfide bonds is incubated with such cells, and the incubate is treated with a reducing agent.
9. The composition of claim 1, wherein said liposomes further contain a ligand attached to a distal end of the hydrophilic polymer chains, said ligand effective for ligand- specifϊc binding to a receptor molecule on a target cell surface prior to chemical release of the hydrophilic polymer chains.
10. The composition of claim 9, wherein said ligand is selected from the group consisting of (i) folate, where the composition is intended for treating tumor cells having cell- surface folate receptors, (ii) pyridoxyl, where the composition is intended for treating virus- infected CD4+ lymphocytes, and (iii) sialyl-Lewisx, where the composition is intended for treating a region of inflammation.
11. The composition of claim 1, wherein the liposomes further include a ligand attached to the liposome surface, said ligand being effective to bind to a target cell surface receptor molecule after, but not before, chemical release of the hydrophilic polymer chains.
12. The composition of claim 1, wherein said liposomes further contain a cationic lipid effective to impart a positive liposome-surface charge, to enhance binding of liposomes to target cells after, but not before, chemical release of the hydrophilic polymer chains.
13. The composition of claim 1, wherein the agent entrapped in the lipid vesicles is a polynucleotide capable of expressing a selected protein, when taken up by a target cell.
14. The composition of claim 1, wherein the agent entrapped in the liposomes is an oligonucleotide or oligonucleotide analog effective for sequence-specific binding to cellular
RNA or DNA.
15. A method of delivering a compound to target cells in a subject comprising parenterally administering to the subject liposomes designed for reaching the target cells via the bloodstream, each liposome containing said compound in entrapped form and having an outer surface coating of chemically releasable hydrophilic polymer chains, and 47 contacting the liposomes at the target cells with a chemical agent effective to release said chains forming said surface coating, thereby to expose hydrophobic polymers on the liposome outer surface for interaction with outer cell membranes of the target cells and promote fusion of the liposome with the target cells.
16. The method of claim 15, wherein said hydrophilic polymer chains are releasably attached to the liposome via a reducible chemical linkage, and said contacting includes administering to the subject a reducing agent effective to release said chains.
17. The method of claim 16, wherein said chemical linkage is a disulfide linkage and said reducing agent is selected from the group consisting of cysteine, glutathione and ascorbate.
18. The method of claim 15, wherein each of said hydrophilic polymer chains is releasably attached to the liposome via a pH sensitive chemical linkage, and said contacting includes targeting the liposomes to a site having a pH effective to release said chains.
19. The method of claim 18, wherein said liposomes have sizes between 0.03-0.40 m for extravasation into a solid tumor.
20. The method of claim 15, wherein said liposomes further contain a ligand attached to a distal end of the hydrophilic polymer chains, said ligand effective for ligand- specific binding to a receptor molecule on a target cell surface before chemical release of the hydrophilic polymer coating.
21. The method of claim 20, wherein said ligand is selected from the group consisting of (i) folate, where the composition is intended for treating tumor cells having cell- surface folate receptors, (ii) pyridoxyl, where the composition is intended for treating virus- infected CD4+ lymphocytes, and (iii) sialyl-Lewisx, where the composition is intended for treating a region of inflammation.
22. The method of claim 15, wherein the liposomes further include a ligand attached to the liposome surface, said ligand being effective to bind to a target cell surface receptor molecule after, but not before, chemical release of the hydrophilic polymer coating.
23. The method of claim 15, wherein said liposomes further contain a cationic lipid effective to impart a positive liposome-surface charge, to enhance binding of liposomes to target cells after, but not before, chemical release of the hydrophilic polymer coating.
24. A method for screening a hydrophobic polymer for fusogenic activity with a target membrane, comprising adding to a suspension of target cells, atriblock copolymer composed of a segment of the hydrophobic polymer to be tested, and attached to each end of the polymer segment through a chemically releasable bond, a hydrophilic polymer segment effective to solubilize the hydrophobic polymer segment in the suspension, releasing said hydrophilic polymers to expose said hydrophobic segments to said target cells; and analyzing said suspension for lysis of said target cells.
25. The method of claim 24, wherein said target cells are erythrocytes.
26. The method of claim 24, wherein said releasable linkage is a disulfide linkage, and said releasing includes adding a reducing agent to the suspension.
27. The method of claim 24, wherein said hydrophilic polymer is polyethylene glycol having a molecular weight between 1,000-5,000 daltons.
28. A polymer-lipid conjugate for use in promoting fusion between target membranes, comprising a first segment composed of a hydrophilic polymer; a second segment composed of a hydrophobic polymer, said second segment joined to said first segment by a chemically releasable bond; and attached to said second segment, a vesicle-forming lipid member. 49
STATEMENT UNDER ARTICLE 19
Claim 1 is amended to include the content of original claim 2; namely that the liposomes each contain a diblock copolymer composed of a hydrophobic polymer chain and a hydrophilic polymer chain. Support for this is inherent in original claim 2, and consistent with Fig. 1 and its description.
Claim 2 is amended to direct the claim to the embodiment where the liposomes further include hydrophilic polymer chains bound to a vesicle- forming lipid via a releasable chain. Basis for this is set forth in Fig. 1 and on page 10, lines 26-27.
Claim 3 is unchanged.
Claims 4 and 5 are amended for consistency with claim 1, by changing the word "coating" to "chains".
Claims 6-8 are unchanged.
Claim 9 is amended to remove the term "unshielded" to clarify that the ligand is attached to a distal end of the hydrophilic polymer chains, as set forth in Fig. 1 and its description.
Claim 10 is unchanged.
Claims 11-12 are amended to remove the term "shielded" to clarify that the ligand (claim 11) is attached to the liposome surface and that the cationic lipid (claim 12) imparts a liposome-surface charge. The word "coating" is replaced with "chains" for consistency with amended claim 1.
Claims 13-19 and 21 are unchanged.
Claims 20. 22. 23 are amended as set forth for claims 9, 11 and 12.
Claim 24 is amended to change "hemolysis" to "lysis", for consistency with the spirit of the claim in that the hydrophobic polymer is added to a suspension of target cells.
Claims 25-28 are unchanged.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK97912775T DK0932391T3 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
EP97912775A EP0932391B1 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
AT97912775T ATE232086T1 (en) | 1996-10-11 | 1997-10-10 | FUSOGENIC LIPOSOME COMPOSITION AND METHODS |
BR9712230-0A BR9712230A (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome method and composition. |
IL12929297A IL129292A0 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
AU49878/97A AU715063B2 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
JP51862998A JP2001504093A (en) | 1996-10-11 | 1997-10-10 | Fusion liposome compositions and methods |
CA002267904A CA2267904C (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
DE69718924T DE69718924T2 (en) | 1996-10-11 | 1997-10-10 | FUSOGENIC LIPOSOME COMPOSITION AND METHOD |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2826996P | 1996-10-11 | 1996-10-11 | |
US60/028,269 | 1996-10-11 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO1998016202A2 WO1998016202A2 (en) | 1998-04-23 |
WO1998016202A3 WO1998016202A3 (en) | 1998-07-16 |
WO1998016202B1 true WO1998016202B1 (en) | 1998-09-03 |
Family
ID=21842486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/018838 WO1998016202A2 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
Country Status (15)
Country | Link |
---|---|
US (1) | US5891468A (en) |
EP (1) | EP0932391B1 (en) |
JP (1) | JP2001504093A (en) |
AT (1) | ATE232086T1 (en) |
AU (1) | AU715063B2 (en) |
BR (1) | BR9712230A (en) |
CA (1) | CA2267904C (en) |
DE (1) | DE69718924T2 (en) |
DK (1) | DK0932391T3 (en) |
ES (1) | ES2191833T3 (en) |
HK (1) | HK1047550A1 (en) |
IL (1) | IL129292A0 (en) |
PT (1) | PT932391E (en) |
TW (1) | TW520297B (en) |
WO (1) | WO1998016202A2 (en) |
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